7. Miles Massey (George Clooney) in Intolerable Cruelty

Picture this – you’ve fallen for a rumored gold digger. You’re financially well-off, but haven’t seen any concrete evidence of exploitation – this being the case, you have reason to believe that there’s more to this person’s story than meets the eye. Giving a relationship a go might be risky, but it isn’t completely out of the question. Miles Massey, on the other hand, defended a gold digger’s ex-husband in court and had access to privileged information that proved she was, in fact, only after his money, but somehow ended up marrying her, nearly getting killed for it, filing for divorce and then asking for a second chanceat romance. I don’t want someone with judgment that hilariously awful anywhere near me in court.